Upper Marlboro is among the oldest of the surviving southern Maryland towns with histories dating back to colonial times. The area was settled around 1695 and named after the first Duke of Marlborough (an ancestor of Winston Churchill). It was established as a port town for tobacco ships in 1706, when the western branch of the Patuxent River was still navigable there. It has been the county seat of Prince George’s County since 1721.

The town is the birthplace of John Carroll, the first Catholic Archbishop in America and founder of Georgetown University, and of his brother Daniel, a signer of the U.S. Constitution. Throughout its history, Upper Marlboro has been the home or place of work of prominent national, state, and local figures. In recent times, it was the home of the late Lansdale G. Sasscer, Sr., Maryland State Senator, 1922–1938, and U.S. Congressman, 1939–1953.

Changing economics have changed the face of the town over the years. Its stature as the main shopping center for a large rural area has been diminished by malls and commercial developments that are closer to its former shoppers. The fields of tobacco that once dominated the countryside have given way to residential and commercial developments; only a few farms remain in the increasingly urban landscape.

Upper Marlboro now hosts the administrative bustle of a county seat by day and relaxes into a quiet country town by night. Though many of its historic structures have been lost through demolition, the remaining old homes and streets reflect the grace and beauty for which the town was known in its earlier days. Retention of that old-town country atmosphere is a continuing resolve of the townspeople and the town commission as they strive to meet the challenges presented by governmental, residential, and commercial development.